The Worst Film Friends Ever

The enabling, jerkwad buddies of 30 Minutes or Less are but the latest in a long line of crappy best friends in film. Here are the 10 Worst Best Friends in Film!

by EDITOR Nov 16th, 2011

Ruben Fleischer's film 30 Minutes or Less is hitting DVD and Blu-Ray today. In the film, Nick (Jesse Eisenberg) and his best friend Chet (Aziz Ansari) not only scheme to rob a bank together (under duress, obviously), but also bicker endlessly about the various relationships they've had with each other's family members, plan to rob cars, and generally spend the length of the film arguing and enabling one another to do all manner of horrific crimes. And they're supposed to be best friends. Some friends. Also in the film is a pair of feckless criminal friends (Danny McBride and Mick Swardson) who are less together, broke, and immoral human beings, but seem to enjoy a much better relationship. Odd that the criminals should get along better than the straight arrows.

When putting pen to paper (fingertip to keyboard?), I find that the phenomenon of “frenemies” is rather common in feature films. The list of best friends who do nothing but offer bad advice, snide put-downs, or just enabling destructive behavior is endless. Good friends are common, of course, and offer positive advice to struggling heroes who are wrestling with romantic (or other) problems, but just as often you'll find some jerkwad ready to advance their own agenda while callously ignoring the hero's feelings. This can be played for laughs or can be seen as the tragedy it is. In high school, thanks to that endless series on in-classroom health films, they warned you about peer pressure. But in the following examples, you get to see such bad best friend behavior put into stark practice.

Here, then, are the ten best examples of toxic friendships from movies.

10. REGINA GEORGE from MEAN GIRLS (2004)

When Cady Heron (Lindsay Lohan) moved from Africa to America, she had to suddenly acclimatize herself to the all-too-familiar pubic school dynamics that we all learned about from a generation of sitcoms. While she was initially wide-eyed and naïve about the experience, she proved to be a quick study, learning the hierarchy of high school girls and falling in with the school's circle of “mean girls,” led by the blithesome and cruel Regina George (Rachel McAdams). Regina proved to be caring toward her friends, and welcoming of Cady… so long as she kept up the status quo, and remained appropriately fashion-obsessed, and 100% deferential to Regina's every whim. Cady only fell in with the Mean Girls in order to operate a brief sociological study, but ended up being corrupted by their vanity nonetheless. There was something attractive and appealing about hanging out with the popular girls. Here is a best friend so insidious, she can corrupt the teen girls who aren't even interested in being their friends. Yeesh.

9. DR. GONZO from FEAR AND LOATHING IN LAS VEGAS (1998)

Ostensibly an attorney for Raoul Duke, the pseudonymous identity for Hunter S. Thompson (Johnny Depp), Dr. Gonzo (Benicio Del Toro, plus 60 pounds) seemed to only exist for the express purpose of giving the perpetually drug-fueled Duke someone to talk to on their dark trip to the heart of the American Dream (i.e. Las Vegas). He would listen to Duke's insane rambling, and seemed, incredibly, to understand what he was talking about. When Duke was coming down off of his bouillabaisse of drugs, it was time for Dr. Gonzo to get hopped up on an entire sheet of LSD, and demand that he be electrocuted during a key moment of “White Rabbit.” The two took turns being the out-of-control one. It seemed to me that Dr. Gonzo was the one who was always prepared to offer even stronger stuff, though (he offers Duke a few drops of something called adrenochrome at one point, leading to one of the film's more embarrassing blackouts). Duke would have taken the drugs on his own, but with an enabler nearby, the two of them reached a level of drug consumption unseen since Sid & Nancy.

8. CHAD from IN THE COMPANY OF MEN (1997)

Howard (Matt Malloy) is kind of a jellyfish. He works in a stifling corporate environment where he doesn't produce anything of merit, and doesn't seem to make any meaningful decisions. Luckily for him, he has Chad to talk to. Chad (Aaron Eckhart, in his breakout role) is a handsome alpha-male type who digs sexual gossip, drinking, and playing the good-old-boys games with Howard. Howard has been heartbroken before, so female-bashing comes all too easily with Chad's prodding. When Chad comes up with a truly devious scheme, Howard reluctantly agrees. Chad's plan is to find a weak-willed woman, have them both seduce her, and then dump her simultaneously, in the hopes of driving her to suicide. Howard is not the seduce-and-destroy type, but, thanks to Chad's overwhelming personality, and casual evilness, Howard is corrupted. A friend who wants you to be evil is not a friend you want to have. Neil LaBute's debut feature is a stirring portrait of the depths of misogyny.

7. BRUNO ANTONY from STRANGERS ON A TRAIN (1951)

Not really a best friend, but a gregarious and friendly fellow, Bruno Antony (Robert Walker) is a devious and death-minded killer who only needs a favor, and then he'll go away. In one of the most famous setups in crime film history, Bruno approaches a stranger on a train, Guy (Farley Granger) and they begin to commiserate about the horrible people in their respective lives. Bruno suggests that they each kill one another's hated victims, belying suspicion; what would their motives be? They have no connection each other, having met randomly without witnesses. Guy chuckles at the simple brilliance of this plan, but dismisses it…until Bruno appears at his doorstep a few days later, announcing that he has gone through on his part of the bargain. Not only does Bruno have blackmail material on Guy, but is now entreating Guy to commit murder himself. And Bruno likes Guy. I'd hate to see what his plans would be if he hated him. Hitchcock's crime thriller, co-written by Raymond Chandler, is twisted and wicked and fun.

6. COREY FELDMAN from JUST ABOUT ANYTHING COREY FELDMAN HAS BEEN IN

I'm very positive on Corey Feldman, as I think he's a talented guy with a definite flair for playing flip and crass weirdos. I always preferred him over that Haim kid, God rest his soul. But a look over Feldman's filmography reveals a disturbing pattern of jerky best friends with a tendency to enable destructive behavior and risk the lives of those around him. In The Goonies he played they mouthy friend who seemed to call attention to his comrades when they wanted to hide. In License to Drive, he encourages his best friend to “borrow” his dad's car for a night of fun with a hot chick, which goes legendarily awry. In Stand By Me he was always the one to start the fights with his more serious friends. He may have been the only one to be willing to take down the vampires in The Lost Boys, but he was a bit sloppy about it, and could have easily killed his best friend on several occasions. Feldman was always funny and always entertaining, but if he was your best friend, it's likely you would constantly be in danger.

5. WITHNAIL from WITHNAIL & I(1987)

It is 1969, and Marwood (Paul McGann) is living in poverty with his friend Withnail (Richard E. Grant). Withnail is noisy, crass, rude, and browbeats Marwood at every possibly opportunity. Withnail fancies himself a free-spirited Bohemian type, but is little more than a foul-mouthed alcoholic. Profanity flows freely out of him, and he seems to have perfected a fashion of cursing that sounds like spitfire poetry. He often has schemes of getting money or finally overcoming his beefs with The Man, but never does anything more than drink and cuss. When Marwood and Withnail move into a country cottage, their friendship begins to stand in stark relief, and the weak-willed Marwood begins to see Withnail for the manipulative sphincter that he is. These two have been friends for so long, neither of them seems to have recognized that their relationship is now one of hateful co-dependence. Few comedies are as dreary and as acidic as Bruce Robinson's Withnail & I, a film that has a vast cult ready to stand behind it. Not like Withnail would do the same for you.

4. NANCY DOWNS from THE CRAFT(1996)

Another tale of an outsider teenage girl moving to a new school, Andrew Fleming's slumber party classic The Craft follows Sarah Bailey (Robin Tunney), a wispy outsider who falls in with a trio of Goth types who, as they fancy themselves, are an operating coven of amateur witches. Apart, the four of them are shy weirdos, but together, they're weirdos who gather in candlelit rooms and entertain fantasies of learning vengeance spells. The queen bee of the coven is Nancy Downs (the wickedly attractive Fairuza Balk), who discovers that their spells actually seem to be working from time to time, and implores her group to invoke the dangerous powers of an evil demon in order to ratchet their magic to new heights. The four of them go through with it, and while their power does increase (Neve Campbell sheds her scar tissue! Robin Tunney finds a date!), Nancy soon transforms into a power-mad ultra-witch with designs on world domination. How do you break it to a friend that you don't want to hang out anymore when they helped you gain superpowers? And that they can, with a flick of the wrist, set you on fire? Nancy is an off-balance outsider friend who turns into a legitimately insane evil witch. She’d be a powerful ally, were she not hell bent on killing you on occasion. Many girls I've spoken to have a deep affection for The Craft and all its bitchy revenge fantasy glory. Some may consider it a legitimate cult film.

3. RANDAL GRAVES from CLERKS (1994)

Dante (Brian O'Halloran) is kind of a whiner, and a bit non-committal about his life's decisions. He has a loving girlfriend that dotes on him, but he doesn't really seem all that committed. He works in a convenience store and seems to have no hope for anything better. Into Dante's life comes his childhood best friend Randal (Jeff Anderson), a flip, openly obscene slacker who seems more at peace with his a**hole status. Randal's modus operandi is to get Dante to come out of his shell, and admit to his open hatred for his situation, but mostly ends up just acting crass in public and embarrassing his best friend. Randall is a nice enough guy, but seems to take too much pleasure in baiting Dante into saying embarrassing stuff; he gets Dante to admit at one point into attempting auto-fellatio. Randal's ultimate motives are noble, and he turns out to be a good friend, but not before casually selling cigarettes to a six-year-old and costing Dante thousands of dollars in fines. Randal cares, but he's got a weird way of showing it. Kevin Smith's slacker polemic launched a thousand indie films, and remains funny to this day.

2. WALTER SOBCHACK from THE BIG LEBOWSKI (1998)

“The Dude” Lebowski (Jeff Bridges) is a lay-about pothead hippie who lives a seemingly blissful life of marijuana use, bowling, and… not much else. He seems unable to understand what is happening in his life from one moment to the next, and is perfectly okay with it. His best bowling buddy is Walter (John Goodman) a perpetually peeved, mountainous Vietnam vet. Walter is a stickler for rules, and pulls a gun on a friend he suspects of cheating at bowling. He's a jerk of the highest order, yelling in public, and treating clerks like dirt. When it comes time for The Dude to take part in a ransom exchange (!), Walter comes along and pretty much forces The Dude to keep the ransom money. This leaves The Dude with a seriously harshed mellow, as he may be responsible for the death of a kidnapped woman. To make things worse, Walter refuses to accept that he had anything to do with the scam, whimsically going back to business as usual, sometimes coming up with non-starter schemes to get the money, which they lost anyway, back. He's a noisy, arrogant blowhard with delusions of grandeur and a persecution complex. Good guy. He confronts The Dude late in the film. “Am I wrong?” he asks. “You're not wrong, Walter,” The Dude shoots back, “you're just an a**hole.” The Coen Bros. have a legitimate cult phenomenon on their hands.

1. DICK HICKOCK from IN COLD BLOOD (1967)

Perry Smith (Robert Blake) is a shiftless drifter, out of a job, and with no ties to the world. He is a sad-eyed little boy in the body of a brooding, clumsy adult. His only friend in the world is Dick Hickock (Scott Wilson) the only person who ever encourages Perry to make anything of his life. The two of them are low on money, and spend the bulk of Richard Brooks' crime classic In Cold Blood searching for ways to make a quick buck. Perry is not really creative enough to think of anything, and only seems to enjoy himself when he's collecting bottles on the side of the road. Dick's only vision of making money has to do with committing a crime. Fans of Truman Capote's novel may be able to intuit why Dick and Perry set their sights on the Clutter family, a peaceful unit of farmers in Kansas, and scoped them for a robbery. The decision to invade their home came from a vicious cycle of mutual encouragement that led to the brutal murder of the entire family, and the eventual conviction and execution of both Dick and Perry. A (here paraphrased) line of dialogue seems to illustrate the power of this toxic friendship best: how do you convict two men for committing a crime they wouldn't have committed individually? With friends like these, right?